After the release of her first EP in 2003, she signed with Universal South Records and toured with Billy Bob Thornton, Jewel, Train, Keith Urban, and Kasey Chambers.

[4] Holly Williams made small musical appearances at this time, one of them joining John C. Reilly in Nashville, Tennessee, to sing "Let's Duet" during the release of Walk Hard: The Dewey Cox Story on December 9, 2007.

After a long break Williams began playing guitar and writing songs again, she signed with Luke Lewis at Mercury Records.

USA Today said "Hank Williams' granddaughter reveals a heart-on-sleeve intensity that might be grating were it not for the purity and potency of her milk-and-whiskey-kissed singing and the catchy clarity and integrity of her songs".

Williams finished a six-week tour in Europe in early 2010, and continued the rest of the year headlining gigs and opening for other artists such as John Hiatt.

Williams was featured on the soundtrack for Flicka singing "Rodeo Road", written by Tom Douglas and Chuck Cannon.

"[6] Mel Gibson met with Williams in Nashville and featured her on The Passion of The Christ soundtrack singing "How Can You Refuse Him Now", written by her grandfather.

This album includes Dierks Bentley, Jakob Dylan, Gwyneth Paltrow and Jackson Browne adding backing harmonies.

"[7] The New York Times stated "Williams is often closer to songwriters like John Prine or Bruce Springsteen, than the smiley Nashville mainstream.

[10] Williams was married on September 27, 2009, to fellow musician Chris Coleman (who co-wrote three of the songs on The Highway) and they settled in Nashville, Tennessee.